#------------------------------------------------------------------------------
#$Date: 2023-09-08 01:56:23 +0300 (Fri, 08 Sep 2023) $
#$Revision: 286269 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/39/7713916.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7713916
loop_
_publ_author_name
'Arruri, Sathyanarayana'
'Réveret, François'
'Jouffret, Laurent'
'Boyer, Damien'
'Chadeyron, Genevieve'
'Cisnetti, Federico'
_publ_section_title
;
 Polymeric copper(I)--NHC complexes with bulky bidentate (N^C) ligands:
 synthesis and solid-state luminescence
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01669B
_journal_year                    2023
_chemical_formula_sum            'C21 H25 Cl Cu N3 O'
_chemical_formula_weight         434.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.387(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3299(15)
_cell_length_b                   9.6126(10)
_cell_length_c                   14.9035(16)
_cell_measurement_reflns_used    12734
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.8430
_cell_measurement_theta_min      1.3823
_cell_volume                     2052.9(4)
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            168008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.965
_diffrn_source                   molybdene
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0286P)²+2.2658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5179
_reflns_number_total             6281
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01669b2.cif
_cod_data_source_block           P21n_CXautre_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7713916
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.581
_shelx_estimated_absorpt_t_max   0.878
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.36603(2) 0.45164(2) 0.32536(2) 0.01109(5) Uani 1 1 d . . . . .
Cl Cl 0.33932(3) 0.51458(5) 0.46555(3) 0.02172(9) Uani 1 1 d . . . . .
O1 O -0.08223(8) 0.38977(12) 0.15925(8) 0.0173(2) Uani 1 1 d . . . . .
N1 N 0.27421(8) 0.61628(13) 0.18210(9) 0.0109(2) Uani 1 1 d . . . . .
N2 N 0.39662(9) 0.51384(14) 0.13425(9) 0.0126(2) Uani 1 1 d . . . . .
N3 N 0.06715(9) 0.75909(13) 0.16249(9) 0.0111(2) Uani 1 1 d . . . . .
C1 C 0.34272(10) 0.52739(15) 0.20896(10) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.28584(11) 0.65925(17) 0.09398(11) 0.0150(3) Uani 1 1 d . . . . .
H2 H 0.247233 0.722136 0.061476 0.018 Uiso 1 1 calc R U . . .
C3 C 0.36294(11) 0.59395(18) 0.06352(11) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.388953 0.601370 0.005258 0.020 Uiso 1 1 calc R U . . .
C4 C 0.19865(10) 0.66071(16) 0.24129(10) 0.0117(3) Uani 1 1 d . . . . .
H4A H 0.207676 0.759881 0.257039 0.014 Uiso 1 1 calc R U . . .
H4B H 0.201563 0.605967 0.297508 0.014 Uiso 1 1 calc R U . . .
C5 C 0.10343(10) 0.64249(16) 0.19859(10) 0.0109(3) Uani 1 1 d . . . . .
C6 C 0.05727(11) 0.51469(16) 0.19736(11) 0.0134(3) Uani 1 1 d . . . . .
C7 C -0.03130(11) 0.51115(17) 0.15742(11) 0.0128(3) Uani 1 1 d . . . . .
C8 C -0.07048(11) 0.63052(17) 0.12030(11) 0.0151(3) Uani 1 1 d . . . . .
C9 C -0.01788(11) 0.75161(17) 0.12398(11) 0.0145(3) Uani 1 1 d . . . . .
H9 H -0.043271 0.833606 0.097921 0.017 Uiso 1 1 calc R U . . .
C10 C 0.09863(13) 0.38519(18) 0.23810(14) 0.0242(4) Uani 1 1 d . . . . .
H10A H 0.050496 0.335471 0.271755 0.036 Uiso 1 1 calc R U . . .
H10B H 0.149892 0.410746 0.278712 0.036 Uiso 1 1 calc R U . . .
H10C H 0.122424 0.325016 0.190356 0.036 Uiso 1 1 calc R U . . .
C11 C -0.16599(12) 0.6308(2) 0.07800(14) 0.0259(4) Uani 1 1 d . . . . .
H11A H -0.183542 0.726266 0.062255 0.039 Uiso 1 1 calc R U . . .
H11B H -0.211264 0.592835 0.120499 0.039 Uiso 1 1 calc R U . . .
H11C H -0.165451 0.573328 0.023679 0.039 Uiso 1 1 calc R U . . .
C12 C -0.06891(14) 0.3046(2) 0.08066(13) 0.0253(4) Uani 1 1 d . . . . .
H12A H -0.111788 0.225289 0.082422 0.038 Uiso 1 1 calc R U . . .
H12B H -0.004423 0.270769 0.079463 0.038 Uiso 1 1 calc R U . . .
H12C H -0.081450 0.360040 0.026712 0.038 Uiso 1 1 calc R U . . .
C13 C 0.47106(10) 0.41300(17) 0.12997(10) 0.0131(3) Uani 1 1 d . . . . .
C14 C 0.45383(11) 0.28640(18) 0.08731(11) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.52229(12) 0.18402(19) 0.09316(12) 0.0194(3) Uani 1 1 d . . . . .
H15 H 0.511352 0.096557 0.065336 0.023 Uiso 1 1 calc R U . . .
C16 C 0.60621(12) 0.2058(2) 0.13846(11) 0.0220(4) Uani 1 1 d . . . . .
C17 C 0.62211(12) 0.3353(2) 0.17673(12) 0.0225(4) Uani 1 1 d . . . . .
H17 H 0.680195 0.352513 0.205750 0.027 Uiso 1 1 calc R U . . .
C18 C 0.55542(11) 0.44108(19) 0.17393(11) 0.0178(3) Uani 1 1 d . . . . .
C19 C 0.57280(13) 0.5779(2) 0.21949(15) 0.0285(4) Uani 1 1 d . . . . .
H19A H 0.552373 0.653818 0.180078 0.043 Uiso 1 1 calc R U . . .
H19B H 0.639613 0.587834 0.232445 0.043 Uiso 1 1 calc R U . . .
H19C H 0.537784 0.581535 0.275692 0.043 Uiso 1 1 calc R U . . .
C20 C 0.36410(12) 0.2597(2) 0.03708(12) 0.0219(3) Uani 1 1 d . . . . .
H20A H 0.311544 0.295398 0.071967 0.033 Uiso 1 1 calc R U . . .
H20B H 0.356390 0.159461 0.027718 0.033 Uiso 1 1 calc R U . . .
H20C H 0.365953 0.306962 -0.021157 0.033 Uiso 1 1 calc R U . . .
C21 C 0.67719(16) 0.0905(3) 0.14641(14) 0.0349(5) Uani 1 1 d . . . . .
H21A H 0.647280 0.007158 0.170924 0.052 Uiso 1 1 calc R U . . .
H21B H 0.727967 0.119875 0.186488 0.052 Uiso 1 1 calc R U . . .
H21C H 0.702423 0.069425 0.086982 0.052 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu N3 119.58(6) . 2_545 ?
C1 Cu Cl 136.39(5) . . ?
N3 Cu Cl 104.03(4) 2_545 . ?
C7 O1 C12 113.06(13) . . ?
C1 N1 C2 112.00(13) . . ?
C1 N1 C4 122.75(13) . . ?
C2 N1 C4 125.25(13) . . ?
C1 N2 C3 111.73(13) . . ?
C1 N2 C13 121.50(13) . . ?
C3 N2 C13 126.29(13) . . ?
C9 N3 C5 118.19(13) . . ?
C9 N3 Cu 119.81(10) . 2 ?
C5 N3 Cu 121.79(10) . 2 ?
N1 C1 N2 103.36(13) . . ?
N1 C1 Cu 128.97(11) . . ?
N2 C1 Cu 127.46(11) . . ?
C3 C2 N1 106.45(14) . . ?
C2 C3 N2 106.45(14) . . ?
N1 C4 C5 112.41(12) . . ?
N3 C5 C6 123.09(14) . . ?
N3 C5 C4 114.64(13) . . ?
C6 C5 C4 122.27(14) . . ?
C5 C6 C7 117.11(14) . . ?
C5 C6 C10 122.53(14) . . ?
C7 C6 C10 120.35(14) . . ?
O1 C7 C8 119.64(14) . . ?
O1 C7 C6 119.47(14) . . ?
C8 C7 C6 120.80(14) . . ?
C9 C8 C7 117.31(14) . . ?
C9 C8 C11 120.54(15) . . ?
C7 C8 C11 122.15(15) . . ?
N3 C9 C8 123.49(15) . . ?
C14 C13 C18 122.16(15) . . ?
C14 C13 N2 118.53(14) . . ?
C18 C13 N2 119.14(15) . . ?
C15 C14 C13 117.78(15) . . ?
C15 C14 C20 120.66(16) . . ?
C13 C14 C20 121.56(15) . . ?
C16 C15 C14 122.06(17) . . ?
C17 C16 C15 118.24(16) . . ?
C17 C16 C21 121.22(18) . . ?
C15 C16 C21 120.53(19) . . ?
C16 C17 C18 122.07(16) . . ?
C17 C18 C13 117.60(16) . . ?
C17 C18 C19 120.90(16) . . ?
C13 C18 C19 121.47(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu C1 1.9087(15) . ?
Cu N3 2.0913(13) 2_545 ?
Cu Cl 2.2111(5) . ?
O1 C7 1.3766(18) . ?
O1 C12 1.442(2) . ?
N1 C1 1.3598(19) . ?
N1 C2 1.388(2) . ?
N1 C4 1.4649(19) . ?
N2 C1 1.366(2) . ?
N2 C3 1.389(2) . ?
N2 C13 1.4430(19) . ?
N3 C9 1.3453(19) . ?
N3 C5 1.3462(19) . ?
C2 C3 1.352(2) . ?
C4 C5 1.512(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.399(2) . ?
C6 C10 1.505(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.388(2) . ?
C8 C11 1.503(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.392(2) . ?
C14 C20 1.506(2) . ?
C15 C16 1.391(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.508(3) . ?
C17 C18 1.396(2) . ?
C18 C19 1.500(3) . ?
